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[ CAS No. 24033-03-2 ] {[proInfo.proName]}

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Chemical Structure| 24033-03-2
Chemical Structure| 24033-03-2
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Product Details of [ 24033-03-2 ]

CAS No. :24033-03-2 MDL No. :MFCD02684153
Formula : C14H13ClO Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 232.71 Pubchem ID :-
Synonyms :

Safety of [ 24033-03-2 ]

Signal Word:Danger Class:8
Precautionary Statements:P264-P270-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P403+P233-P501 UN#:3261
Hazard Statements:H302-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 24033-03-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 24033-03-2 ]

[ 24033-03-2 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 24033-03-2 ]
  • [ 1860-58-8 ]
YieldReaction ConditionsOperation in experiment
75% With sodium hydroxide In methanol at 55℃; for 4h;
Multi-step reaction with 2 steps 1: 98 percent / dimethylformamide / 2 h / 100 °C 2: 98 percent / NaOH / H2O / Heating
  • 2
  • [ 1700-30-7 ]
  • [ 24033-03-2 ]
YieldReaction ConditionsOperation in experiment
94% With thionyl chloride In dichloromethane at 0℃; for 3h;
80% With thionyl chloride In benzene for 2.5h; Heating;
67% With methanesulfonyl chloride; triethylamine In dichloromethane at 0℃; 2 To a solution of 3-benzyloxybenzyl alcohol (3.0g, 14.0mmol) in dichloromethane (30mL) was added methanesulfonyl chloride (1.39mL, 16.8mmol) and triethylamine (2.34mL, 16.8mmol) on an ice bath, and the solution was stirred overnight. The reaction solution was diluted with dichloromethane, washed with aqueous solution of 5% sodium bicarbonate, and then, dried over anhydrous magnesium sulfate. The solvent was evaporated, then, the residue was purified by silica gel column chromatography (hexane : ethyl acetate = 10 : 1), and 1-benzyloxy-3-chloromethyl-benzene (2.2g, 67%) was obtained as a colorless oil. Next, to a solution of iminodicarboxylic acid di-tert-butyl ester (2.12g, 8.76mmol) in N,N-dimethylformamide (13mL) was added sodium hydride (0.39g, 9.86mmol, 60% in oil), the solution was stirred at 60°C for 6 hours, 1-benzyloxy-3-chloromethyl-benzene (1.0g, 4.30mmol) was added, and the solution was further stirred at 60°C for 4 hours. The reaction solution was allowed to room temperature, then, dichloromethane and water were added for partitioning, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated, then, the residue was purified by silica gel column chromatography (hexane : ethyl acetate =10:1), and (3-benzyloxybenzyl) iminodicarboxylic acid di-tert-butyl ester (691 mg, 39%) was obtained as a pale yellow oil. Lastly, (3-benzyloxybenzyl) iminodicarboxylic acid di-tert butyl ester (691 mg, 1.67mmol) was cooled on an ice bath, trifluoroacetic acid (3mL) was added, and the solution was stirred for 30 minutes. An aqueous solution of saturated sodium bicarbonate was added to the reaction solution, which was then extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the title compound (292mg, 82%) was obtained as a white waxy solid. This was used in the next reaction without further purification.
With pyridine; thionyl chloride
With thionyl chloride
With thionyl chloride In dichloromethane for 0.5h;
With thionyl chloride In 1,4-dioxane at 20℃;
With thionyl chloride In dichloromethane; N,N-dimethyl-formamide at 40℃; for 4h;
8.66 g With thionyl chloride In dichloromethane at 0℃; for 3h; 3.3. 1-(Benzyloxy)-3-(chloromethyl)benzene (18) To a solution of above product 17 (9.37 g, 43.8 mmol) in DCM (150 mL) at 0 was added thionyl chloride (4.8 mL, 65.7 mmol) and stirred at the same temperature for 3 h. the reaction mixture was concentrated in vacuo and the residue was purified by chromatography (petroleum ether/ethyl acetate, 10/1) to afford 18 (8.66 g, 85% for two steps) as colorless oil.
With thionyl chloride In dichloromethane; N,N-dimethyl-formamide at 20 - 40℃; for 4h; 4.1.2. General synthetic procedure for target compounds 1-4 General procedure: To a solution of the obtained benzyl alcohol 2a (1 equiv) in dichloromethane(20 ml) was slowly added thionyl chloride (6 equiv) anda catalytic amount of DMF at room temperature. After stirring at 40 °Cfor 4 h, the reaction was concentrated under reduced pressure. Theresidue was purified by silica gel column chromatography using amixture of petroleum ether/ethyl acetate (20:1, v/v) as eluent to affordthe desired product 3a. To a solution of the obtained chlorinated intermediates3a (1 equiv) and 4a (1.1 equiv) in acetone was addedK2CO3 (2 equiv) and a catalytic amount of KI at room temperature. Thereaction mixture was heated to 60 °C with stirring overnight. Then thereaction mixture was cooled to room temperature followed by filtrationand the filtrate was concentrated under vacuum. The residue waspurified by silica gel column chromatography using a mixture of petroleumether/ethyl acetate (5:1, v/v) as eluent to afford a white solid.To a solution of the obtained solid (1 equiv) in 2:3:1 THF/MeOH/H2O(18 ml) was added LiOH·H2O (1.5 equiv). After stirring at room temperaturefor 4 h, the volatiles were removed under reduced pressure.The residue was acidified with 1 N hydrochloric acid solution, and thenfiltered and the filter cake was washed with 5 ml of water, dried invacuum to afford a white powder. Recrystallization from EtOH gave thetarget compounds as colorless crystals.

Reference: [1]Lee, Jeewoo; Lee, Ju-Hyun; Kim, Su Yeon; Perry, Nicholas A.; Lewin, Nancy E.; Ayres, Jolene A.; Blumberg, Peter M. [Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 6, p. 2022 - 2031]
[2]Ono; Katsube [Chemical and Pharmaceutical Bulletin, 1983, vol. 31, # 4, p. 1267 - 1276]
[3]Current Patent Assignee: EISAI CO LTD - EP1669348, 2006, A1 Location in patent: Page/Page column 77
[4]France,D.J. et al. [Tetrahedron, 1969, vol. 25, p. 4011 - 4022]
[5]Kametani,T. et al. [Journal of the Chemical Society. Perkin transactions I, 1973, p. 471 - 472] Pinder; Burger; Ariens [Arzneimittel-Forschung/Drug Research, 1970, vol. 20, # 2, p. 245 - 246]
[6]Kelley, James L.; Krochmal, Mark P.; Linn, James A.; McLean, Ed W.; Soroko, Francis E. [Journal of Medicinal Chemistry, 1988, vol. 31, # 3, p. 606 - 612]
[7]Lisowski, Vincent; Enguehard, Cecile; Lancelot, Jean-Charles; Caignard, Daniel-Henri; Lambel, Stephanie; Leonce, Stephane; Pierre, Alain; Atassi, Ghanem; Renard, Pierre; Rault, Sylvain [Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 16, p. 2205 - 2208]
[8]Li, Zheng; Yang, Jianyong; Gu, Weijie; Cao, Guoshen; Fu, Xiaoting; Sun, Xuedan; Zhang, Yu; Jin, Hui; Huang, Wenlong; Qian, Hai [RSC Advances, 2016, vol. 6, # 52, p. 46356 - 46365]
[9]Bi, Fangchao; Ji, Shengli; Venter, Henrietta; Liu, Jingru; Semple, Susan J.; Ma, Shutao [Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 5, p. 884 - 891]
[10]Li, Zheng; Chen, Yueming; Zhang, Yuhan; Jiang, Hongwei; Liu, Yanzhi; Chen, Yufang; Zhang, Luyong; Qian, Hai [Bioorganic Chemistry, 2018, vol. 80, p. 296 - 302]
  • 4
  • [ 24033-03-2 ]
  • [ 13435-20-6 ]
  • [ 20967-96-8 ]
  • 5
  • [ 24033-03-2 ]
  • [ 20967-96-8 ]
YieldReaction ConditionsOperation in experiment
In dimethyl sulfoxide; EXAMPLE 97 A solution of sodium cyanide (5.9 g.) in dimethyl sulphoxide (40 ml.) was treated with 3-benzyloxybenzyl chloride (23.2 g.) and the reaction mixture stirred and maintained at 60 for 1 hour. The mixture was poured into water and the product was isolated with ether in the usual manner to give 3-benzyloxyphenylacetonitrile, b.p. 162-166/0.55 mm.
  • 6
  • [ 1700-30-7 ]
  • [ 124-63-0 ]
  • [ 24033-03-2 ]
YieldReaction ConditionsOperation in experiment
67% Stage #1: (3-(benzyloxy)phenyl)methanol; methanesulfonyl chloride With triethylamine In dichloromethane at 0 - 20℃; Stage #2: With sodium hydrogencarbonate In dichloromethane; water 2 Preparation Example 2. 3-Benzyloxybenzylamine To a solution of 3-benzyloxybenzyl alcohol (3.0g, 14.0mmol) in dichloromethane (30mL) was added methanesulfonyl chloride (1.39mL, 16.8mmol) and triethylamine (2.34mL, 16.8mmol) on an ice bath, and the solution was stirred overnight. The reaction solution was diluted with dichloromethane, washed with aqueous solution of 5% sodium bicarbonate, and then, dried over anhydrous magnesium sulfate. The solvent was evaporated, then, the residue was purified by silica gel column chromatography (hexane : ethyl acetate = 10 : 1), and 1-benzyloxy-3-chloromethyl-benzene (2.2g, 67%) was obtained as a colorless oil. Next, to a solution of iminodicarboxylic acid di-tert-butyl ester (2.12g, 8.76mmol) in N,N-dimethylformamide (13mL) was added sodium hydride (0.39g, 9.86mmol, 60% in oil), the solution was stirred at 60°C for 6 hours, 1-benzyloxy-3-chloromethyl-benzene (1.0g, 4.30mmol) was added, and the solution was further stirred at 60°C for 4 hours. The reaction solution was allowed to room temperature, then, dichloromethane and water were added for partitioning, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated, then, the residue was purified by silica gel column chromatography (hexane : ethyl acetate = 10 : 1), and (3-benzyloxybenzyl) iminodicarboxylic acid di-tert-butyl ester (691 mg, 39%) was obtained as a pale yellow oil. Lastly, (3-benzyloxybenzyl) iminodicarboxylic acid di-tert-butyl ester (691 mg, 1.67mmol) was cooled on an ice bath, trifluoroacetic acid (3mL) was added, and the solution was stirred for 30 minutes. An aqueous solution of saturated sodium bicarbonate was added to the reaction solution, which was then extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the title compound (292mg, 82%) was obtained as a white waxy solid. This was used in the next reaction without further purification.
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